Sodium hydride → HCID 69280764, compound

HRID 1396242Notes

Reaction equation

HRID 1396242 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19]([CH3:23])[C:20](=[O:22])[O-:21])[S:16]2)[C@@H:12]([OH:24])[C@@H:11]1[OH:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1>CN(C=O)C>[Si:1]([O:8][CH2:9][C@H:10]1[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19]([CH3:23])[C:20](=[O:21])[O:22][C:4]([CH3:7])([CH3:6])[CH3:5])[S:16]2)[C@@H:12]([O:24][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C@@H:11]1[O:25][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 86701102HCID 86701102, compound

Product 1

HCID 69280764HCID 69280764, compoundYield 135.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3aR,5R,6S,7R,7aR)-5-((tert-butyldimethylsilyloxy)methyl)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(methyl)carbamate (20 g, 45 mmol) in DMF (150 mL) was added sodium hydride (10.7 g, 446 mmol) in portion at 0° C., and followed by addition of 1-(bromomethyl)-4-methoxybenzene (36 g, 179 mmol). The resulting solution was stirred for 2 h at room temperature, quenched with cold water (200 mL), and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine (5×200 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to afford a residue, which was purified by silica gel column, eluted with 10% ethyl acetate in petroleum ether to give compound 27 as a yellow liquid (21 g, 68%). (ES, m/z): [M+H]+ 689.1. 1H NMR (300 MHz, CDCl3) δ 7.31-7.37 (m, 2H), 7.22-7.28 (m, 2H), 6.10-6.12 (d, J=6.9 Hz, 1H), 4.60-4.74 (m, 4H), 4.20-4.47 (m, 4H), 3.82 (s, 6H), 3.69 (s, 3H), 3.33-3.37 (m, 2H), 1.56 (s, 9H), 0.89 (s, 9H), 0.05 (s, 6H).

Workup

  1. customquenched with cold water (200 mL)
  2. extractionextracted with ethyl acetate (3×500 mL)
  3. washThe combined organic layers were washed with brine (5×200 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto afford a residue, which
  7. customwas purified by silica gel column
  8. washeluted with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-e4b262a73d8e4cae9db76dfd6a094e9e
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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